Ended up getting it working by adding a custom class, tracking, and position: fixed:
Javascript:
$(function () {
$(document).tooltip({
items: ".entry",
position: {
my: "right bottom+50"
},
tooltipClass: "entry-tooltip-positioner",
track: true,
content: function () {
var element = $(this);
if ((element.is(".entry"))) {
return "<div class='hi'>This is a very nice entry! It's so pretty and I feel like I can touch it. This is just random filler text.</div>";
}
}
});
});
CSS:
.entry {
position: relative;
right: -200px;
width: 500px;
}
.entry-tooltip-positioner {
position: fixed !important;
left: -130px !important;
}
And the updated JSFiddle
Hopefully this helps someone else out sometime.